EP3892268A1 - Utilisation de vidofludimus pour le traitement des infections à coronavirus - Google Patents

Utilisation de vidofludimus pour le traitement des infections à coronavirus Download PDF

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Publication number
EP3892268A1
EP3892268A1 EP20315150.1A EP20315150A EP3892268A1 EP 3892268 A1 EP3892268 A1 EP 3892268A1 EP 20315150 A EP20315150 A EP 20315150A EP 3892268 A1 EP3892268 A1 EP 3892268A1
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Prior art keywords
vidofludimus
treatment
subject
coronavirus
sars
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EP20315150.1A
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German (de)
English (en)
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EP3892268B1 (fr
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designation of the inventor has not yet been filed The
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Aix Marseille Universite
Centre National de la Recherche Scientifique CNRS
Universite Claude Bernard Lyon 1 UCBL
Institut National de la Sante et de la Recherche Medicale INSERM
Ecole Normale Superieure de Lyon
Institut de Recherche pour le Developpement IRD
Original Assignee
Aix Marseille Universite
Centre National de la Recherche Scientifique CNRS
Universite Claude Bernard Lyon 1 UCBL
Institut National de la Sante et de la Recherche Medicale INSERM
Ecole Normale Superieure de Lyon
Institut de Recherche pour le Developpement IRD
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Application filed by Aix Marseille Universite, Centre National de la Recherche Scientifique CNRS, Universite Claude Bernard Lyon 1 UCBL, Institut National de la Sante et de la Recherche Medicale INSERM, Ecole Normale Superieure de Lyon, Institut de Recherche pour le Developpement IRD filed Critical Aix Marseille Universite
Priority to EP20315150.1A priority Critical patent/EP3892268B1/fr
Priority to ES20315150T priority patent/ES2928418T3/es
Priority to US17/995,809 priority patent/US20230146096A1/en
Priority to PCT/EP2021/059266 priority patent/WO2021204985A1/fr
Publication of EP3892268A1 publication Critical patent/EP3892268A1/fr
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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
    • A61K31/19—Carboxylic acids, e.g. valproic acid
    • A61K31/192—Carboxylic acids, e.g. valproic acid having aromatic groups, e.g. sulindac, 2-aryl-propionic acids, ethacrynic acid 
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
    • A61K31/19—Carboxylic acids, e.g. valproic acid
    • A61K31/195—Carboxylic acids, e.g. valproic acid having an amino group
    • A61K31/196—Carboxylic acids, e.g. valproic acid having an amino group the amino group being directly attached to a ring, e.g. anthranilic acid, mefenamic acid, diclofenac, chlorambucil
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/53—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with three nitrogens as the only ring hetero atoms, e.g. chlorazanil, melamine
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/12—Antivirals
    • A61P31/14—Antivirals for RNA viruses
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/12—Antivirals
    • A61P31/20—Antivirals for DNA viruses

Definitions

  • the present invention is in the field of medicine, in particular virology.
  • Coronaviridae is a family of enveloped, positive-sense, single-stranded RNA viruses.
  • the viral genome is 26-32 kilobases in length.
  • the particles are typically decorated with large ( ⁇ 20 nm), club- or petal-shaped surface projections (the "peplomers” or “spikes”), which in electron micrographs of spherical particles create an image reminiscent of the solar corona.
  • peplomers club- or petal-shaped surface projections
  • the World Health Organization has named the severe pneumonia caused by this new coronavirus COVID-19 (for Corona Virus Disease 2019, WHO, 2020 ).
  • the present invention relates to use of Vidofludimus for the treatment of coronavirus infections.
  • Vidofludimus is suitable for inhibiting replication of coronavirus and thus would be suitable for the treatment of infections mediated by said type of virus.
  • the present invention relates to a method of treating a coronavirus infection in a subject in need thereof comprising administrating to the subject a therapeutically effective amount of Vidofludimus.
  • coronavirus has its general meaning in the art and refers to any member of members of the Coronaviridae family.
  • Coronavirus is a virus whose genome is plus-stranded RNA of about 27 kb to about 33 kb in length depending on the particular virus.
  • the virion RNA has a cap at the 5' end and a poly A tail at the 3' end.
  • the length of the RNA makes coronaviruses the largest of the RNA virus genomes.
  • coronavirus RNAs encode: (1) an RNA-dependent RNA polymerase; (2) N-protein; (3) three envelope glycoproteins; plus (4) three non-structural proteins. These coronaviruses infect a variety of mammals and birds.
  • Coronaviruses are transmitted by aerosols of respiratory secretions. Coronaviruses are exemplified by, but not limited to, human enteric coV (ATCC accession # VR-1475), human coV 229E (ATCC accession # VR-740), human coV OC43 (ATCC accession # VR-920), Middle East respiratory syndrome-related coronavirus (MERS-Cov) and SARS-coronavirus (Center for Disease Control), in particular SARS-Cov1 and SARS-Cov2.
  • human enteric coV ATCC accession # VR-1475
  • human coV 229E ATCC accession # VR-740
  • human coV OC43 ATCC accession # VR-920
  • MERS-Cov Middle East respiratory syndrome-related coronavirus
  • SARS-coronavirus Center for Disease Control
  • Vidofludimus is particularly suitable for inhibiting the replication of the coronavirus as demonstrated in EXAMPLE.
  • the method of the present invention is suitable for the treatment of Severe Acute Respiratory Syndrome (SARS). More particularly, the method of the present invention is suitable for the treatment of COVID-19.
  • SARS Severe Acute Respiratory Syndrome
  • the subject can be human or any other animal (e.g., birds and mammals) susceptible to coronavirus infection (e.g. domestic animals such as cats and dogs; livestock and farm animals such as horses, cows, pigs, chickens, etc.).
  • said subject is a mammal including a non-primate (e.g., a camel, donkey, zebra, cow, pig, horse, goat, sheep, cat, dog, rat, and mouse) and a primate (e.g., a monkey, chimpanzee, and a human).
  • the subject is a non-human animal.
  • the subject is a farm animal or pet.
  • the subject is a human.
  • the subject is a human infant. In some embodiments, the subject is a human child. In some embodiments, the subject is a human adult. In some embodiments, the subject is an elderly human. In some embodiments, the subject is a premature human infant.
  • treatment refers to both prophylactic or preventive treatment as well as curative or disease modifying treatment, including treatment of patient at risk of contracting the disease or suspected to have contracted the disease as well as patients who are ill or have been diagnosed as suffering from a disease or medical condition, and includes suppression of clinical relapse.
  • the treatment may be administered to a patient having a medical disorder or who ultimately may acquire the disorder, in order to prevent, cure, delay the onset of, reduce the severity of, or ameliorate one or more symptoms of a disorder or recurring disorder, or in order to prolong the survival of a patient beyond that expected in the absence of such treatment.
  • therapeutic regimen is meant the pattern of treatment of an illness, e.g., the pattern of dosing used during therapy.
  • a therapeutic regimen may include an induction regimen and a maintenance regimen.
  • the phrase “induction regimen” or “induction period” refers to a therapeutic regimen (or the portion of a therapeutic regimen) that is used for the initial treatment of a disease.
  • the general goal of an induction regimen is to provide a high level of drug to a patient during the initial period of a treatment regimen.
  • An induction regimen may employ (in part or in whole) a "loading regimen", which may include administering a greater dose of the drug than a physician would employ during a maintenance regimen, administering a drug more frequently than a physician would administer the drug during a maintenance regimen, or both.
  • maintenance regimen refers to a therapeutic regimen (or the portion of a therapeutic regimen) that is used for the maintenance of a patient during treatment of an illness, e.g., to keep the patient in remission for long periods of time (months or years).
  • a maintenance regimen may employ continuous therapy (e.g., administering a drug at a regular interval, e.g., weekly, monthly, yearly, etc.) or intermittent therapy (e.g., interrupted treatment, intermittent treatment, treatment at relapse, or treatment upon achievement of a particular predetermined criteria [e.g., pain, disease manifestation, etc.]).
  • Vidofludimus has its general meaning in the art and refers to 2-[[2-fluoro-4-(3-methoxyphenyl)phenyl]carbamoyl]cyclopentene-1-carboxylic acid.
  • the CAS number is 717824-30-1.
  • Vidofludimus is commercially available from very different sources. Any pharmaceutically acceptable salt of said compound is also encompassed by the term “Vidofludimus”.
  • pharmaceutically acceptable salts includes salts of the compound of the present invention derived from the combination of such compounds with non-toxic acid or base addition salts.
  • Acid addition salts include inorganic acids such as hydrochloric, hydrobromic, hydroiodic, sulfuric, nitric and phosphoric acid, as well as organic acids such as acetic, citric, propionic, tartaric, glutamic, salicylic, oxalic, methanesulfonic, paratoluenesulfonic, succinic, and benzoic acid, and related inorganic and organic acids.
  • inorganic acids such as hydrochloric, hydrobromic, hydroiodic, sulfuric, nitric and phosphoric acid
  • organic acids such as acetic, citric, propionic, tartaric, glutamic, salicylic, oxalic, methanesulfonic, paratoluenesulfonic, succinic, and benzoic acid, and related inorganic and organic acids.
  • Base addition salts include those derived from inorganic bases such as ammonium and alkali and alkaline earth metal hydroxides, carbonates, bicarbonates, and the like, as well as salts derived from basic organic amines such as aliphatic and aromatic amines, aliphatic diamines, hydroxy alkamines, and the like.
  • bases useful in preparing the salts of this invention thus include ammonium hydroxide, potassium carbonate, sodium bicarbonate, calcium hydroxide, methylamine, diethylamine, ethylenediamine, cyclohexylamine, ethanolamine and the like.
  • the compound of the present invention is Vidofludimus calcium also named IMU-838.
  • Vidofludimus is be administered to the subject in combination with at least one other therapeutic agent, preferably in combination with at least one other antiviral agent, more preferably in combination with at least one other antiviral agent selected from the group consisting of remdesivir, lopinavir, ritonavir, hydroxycholoroquine, and chloroquine
  • Vidofludimus is administered to the subject with a therapeutically effective amount.
  • a “therapeutically effective amount” of Vidofludimus is meant a sufficient amount of the compound to treat a coronavirus infection at a reasonable benefit/risk ratio applicable to any medical treatment. It will be understood, however, that the total daily usage of the compounds and compositions of the present invention will be decided by the attending physician within the scope of sound medical judgment.
  • the specific therapeutically effective dose level for any particular patient will depend upon a variety of factors including the disorder being treated and the severity of the disorder; activity of the specific compound employed; the specific composition employed, the age, body weight, general health, sex and diet of the patient; the time of administration, route of administration, and rate of excretion of the specific compound employed; the duration of the treatment; drugs used in combination with the specific agonist employed; and like factors well known in the medical arts.
  • the daily dosage of the products may be varied over a wide range from 0.01 to 1,000 mg per adult per day.
  • the compositions contain 0.01, 0.05, 0.1, 0.5, 1.0, 2.5, 5.0, 10.0, 15.0, 25.0, 50.0, 100, 250 and 500 mg of the active ingredient for the symptomatic adjustment of the dosage to the patient to be treated.
  • a medicament typically contains from about 0.01 mg to about 500 mg of the active ingredient, preferably from 1 mg to about 100 mg of the active ingredient.
  • An effective amount of the drug is ordinarily supplied at a dosage level from 0.0002 mg/kg to about 20 mg/kg of body weight per day, especially from about 0.001 mg/kg to 7 mg/kg of body weight per day.
  • Vidofludimus may be combined with pharmaceutically acceptable excipients, and optionally sustained-release matrices, such as biodegradable polymers, to form therapeutic compositions.
  • pharmaceutically acceptable excipients such as a carboxylate, a carboxylate, a carboxylate, a carboxylate, a carboxylate, a carboxylate, a carboxylate, a carboxylate, a carboxylate, a carboxysulfate, or adiluent, encapsulating material or formulation auxiliary of any type.
  • the active principle in the pharmaceutical compositions of the present invention for oral, sublingual, subcutaneous, intramuscular, intravenous, transdermal, local or rectal administration, can be administered in a unit administration form, as a mixture with conventional pharmaceutical supports, to animals and human beings.
  • Suitable unit administration forms comprise oral-route forms such as tablets, gel capsules, powders, granules and oral suspensions or solutions, sublingual and buccal administration forms, aerosols, implants, subcutaneous, transdermal, topical, intraperitoneal, intramuscular, intravenous, subdermal, transdermal, intrathecal and intranasal administration forms and rectal administration forms.
  • Galenic adaptations may be done for specific delivery in the small intestine or colon.
  • the pharmaceutical compositions contain vehicles which are pharmaceutically acceptable for a formulation capable of being injected.
  • vehicles which are pharmaceutically acceptable for a formulation capable of being injected.
  • These may be in particular isotonic, sterile, saline solutions (monosodium or disodium phosphate, sodium, potassium, calcium or magnesium chloride and the like or mixtures of such salts), or dry, especially freeze-dried compositions which upon addition, depending on the case, of sterilized water or physiological saline, permit the constitution of injectable solutions.
  • the pharmaceutical forms suitable for injectable use include sterile aqueous solutions or dispersions; formulations including sesame oil, peanut oil or aqueous propylene glycol ; and sterile powders for the extemporaneous preparation of sterile injectable solutions or dispersions.
  • the form In all cases, the form must be sterile and must be fluid to the extent that easy syringability exists. It must be stable under the conditions of manufacture and storage and must be preserved against the contaminating action of microorganisms, such as bacteria and fungi.
  • Solutions comprising the compound of the invention as free base or pharmacologically acceptable salts can be prepared in water suitably mixed with a surfactant, such as hydroxypropylcellulose. Dispersions can also be prepared in glycerol, liquid polyethylene glycols, and mixtures thereof and in oils. Under ordinary conditions of storage and use, these preparations contain a preservative to prevent the growth of microorganisms.
  • the compound of the invention can be formulated into a composition in a neutral or salt form.
  • Pharmaceutically acceptable salts include the acid addition salts (formed with the free amino groups of the protein) and which are formed with inorganic acids such as, for example, hydrochloric or phosphoric acids, or such organic acids as acetic, oxalic, tartaric, mandelic, and the like. Salts formed with the free carboxyl groups can also be derived from inorganic bases such as, for example, sodium, potassium, ammonium, calcium, or ferric hydroxides, and such organic bases as isopropylamine, trimethylamine, histidine, procaine and the like.
  • inorganic acids such as, for example, hydrochloric or phosphoric acids, or such organic acids as acetic, oxalic, tartaric, mandelic, and the like.
  • Salts formed with the free carboxyl groups can also be derived from inorganic bases such as, for example, sodium, potassium, ammonium, calcium, or ferric hydroxides, and such organic bases as isopropylamine, trimethylamine,
  • the carrier can also be a solvent or dispersion medium containing, for example, water, ethanol, polyol (for example, glycerol, propylene glycol, and liquid polyethylene glycol, and the like), suitable mixtures thereof, and vegetables oils.
  • the proper fluidity can be maintained, for example, by the use of a coating, such as lecithin, by the maintenance of the required particle size in the case of dispersion and by the use of surfactants.
  • the prevention of the action of microorganisms can be brought about by various antibacterial and antifusoluble agents, for example, parabens, chlorobutanol, phenol, sorbic acid, thimerosal, and the like.
  • isotonic agents for example, sugars or sodium chloride.
  • Prolonged absorption of the injectable compositions can be brought about by the use in the compositions of agents delaying absorption, for example, aluminium monostearate and gelatin.
  • Sterile injectable solutions are prepared by incorporating the active polypeptides in the required amount in the appropriate solvent with various of the other ingredients enumerated above, as required, followed by filtered sterilization.
  • dispersions are prepared by incorporating the various sterilized active ingredients into a sterile vehicle which contains the basic dispersion medium and the required other ingredients from those enumerated above.
  • sterile powders for the preparation of sterile injectable solutions
  • the preferred methods of preparation are vacuum-drying and freeze-drying techniques which yield a powder of the active ingredient plus any additional desired ingredient from a previously sterile-filtered solution thereof.
  • solutions will be administered in a manner compatible with the dosage formulation and in such amount as is therapeutically effective.
  • the formulations are easily administered in a variety of dosage forms, such as the type of injectable solutions described above, but drug release capsules and the like can also be employed.
  • parenteral administration in an aqueous solution for example, the solution should be suitably buffered if necessary and the liquid diluent first rendered isotonic with sufficient saline or glucose.
  • aqueous solutions are especially suitable for intravenous, intramuscular, subcutaneous and intraperitoneal administration.
  • sterile aqueous media which can be employed will be known to those of skill in the art in light of the present disclosure.
  • one dosage could be dissolved in 1 ml of isotonic NaCl solution and either added to 1000 ml of hypodermoclysis fluid or injected at the proposed site of infusion. Some variation in dosage will necessarily occur depending on the condition of the subject being treated. The person responsible for administration will, in any event, determine the appropriate dose for the individual subject.
  • the compound of the invention may be formulated within a therapeutic mixture to comprise about 0.0001 to 1.0 milligrams, or about 0.001 to 0.1 milligrams, or about 0.1 to 1.0 or even about 10 milligrams per dose or so. Multiple doses can also be administered.
  • other pharmaceutically acceptable forms include, e.g. tablets or other solids for oral administration; liposomal formulations ; time release capsules ; and any other form currently used.
  • FIGURES are a diagrammatic representation of FIGURES.
  • FIG. 1 Effects of Remdesivir (A), and Vidofludimus (B) on the replication of SARS-CoV-2 after two days of culture in Vero cells. The effects on SARS-CoV-2 replication are expressed as percentages of non-treated cultures. Dash lines indicate the EC50 and EC90 inhibition values.
  • SARS-CoV-2 strain BavPatl was obtained from Pr Drosten through EVA GLOBAL (https://www.european-virus-archive.com/).
  • Remdesivir GS-5734
  • BLDpharm China.
  • Vidofludimus was also purchased
  • Vero E6 cells were seeded in 100 ⁇ l assay medium (containing 2.5 % fetal calf serum [FCS]) in 96-well plates. The next day, eight 2 fold serial dilutions of compounds, in triplicates were added to the cells (25 ⁇ l/well, in 2.5 % FCS-containing medium). Four virus control wells (per virus) were supplemented with 25 ⁇ L medium and four cell control wells were supplemented with 50 ⁇ l of medium. After 15 min, 25 ⁇ l of a virus mix diluted in medium was added to the wells at the correct MOI (0.002), determined so that the replication growth is still in the log growth curve for the readout at day 2.
  • MOI fetal calf serum
  • the 50% and 90% effective concentrations (EC50, EC90; the compound concentration that is required to inhibit viral RNA replication by 50% and 90 %) were determined using logarithmic interpolation.
  • Vidofludimus has lower EC50 than teriflunomide ( Figure 1B ; 23.06 ⁇ M ). All together the data indicate that Vidofludimus can repress the replication of SARS-CoV-2 in a significant manner and thus is suitable for the treatment of coronavirus infection.

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Virology (AREA)
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  • Molecular Biology (AREA)
  • Communicable Diseases (AREA)
  • Oncology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
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  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
EP20315150.1A 2020-04-10 2020-04-10 Utilisation de vidofludimus pour le traitement des infections à coronavirus Active EP3892268B1 (fr)

Priority Applications (4)

Application Number Priority Date Filing Date Title
EP20315150.1A EP3892268B1 (fr) 2020-04-10 2020-04-10 Utilisation de vidofludimus pour le traitement des infections à coronavirus
ES20315150T ES2928418T3 (es) 2020-04-10 2020-04-10 Uso de vidofludimus para el tratamiento de infecciones por coronavirus
US17/995,809 US20230146096A1 (en) 2020-04-10 2021-04-09 Use of vidofludimus for the treatment of coronavirus infections
PCT/EP2021/059266 WO2021204985A1 (fr) 2020-04-10 2021-04-09 Utilisation de vidofludimus dans le traitement des infections à coronavirus

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
EP20315150.1A EP3892268B1 (fr) 2020-04-10 2020-04-10 Utilisation de vidofludimus pour le traitement des infections à coronavirus

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EP3892268A1 true EP3892268A1 (fr) 2021-10-13
EP3892268B1 EP3892268B1 (fr) 2022-08-17

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Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2015154820A1 (fr) * 2014-04-11 2015-10-15 Panoptes Pharma Gmbh Agents anti-inflammatoires utilisés comme composés virostatiques
US20180015153A1 (en) * 2016-07-16 2018-01-18 Florida State University Research Foundation, Inc. Compounds and methods for treatment and prevention of flavivirus infection
WO2019101888A1 (fr) * 2017-11-23 2019-05-31 Immunic Ag Posologie de vidofludimus à utiliser dans la prévention ou le traitement de maladies inflammatoires chroniques et/ou auto-immunes

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2015154820A1 (fr) * 2014-04-11 2015-10-15 Panoptes Pharma Gmbh Agents anti-inflammatoires utilisés comme composés virostatiques
US20180015153A1 (en) * 2016-07-16 2018-01-18 Florida State University Research Foundation, Inc. Compounds and methods for treatment and prevention of flavivirus infection
WO2019101888A1 (fr) * 2017-11-23 2019-05-31 Immunic Ag Posologie de vidofludimus à utiliser dans la prévention ou le traitement de maladies inflammatoires chroniques et/ou auto-immunes

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
YANYAN DIAO ET AL: "Discovery of Diverse Human Dihydroorotate Dehydrogenase Inhibitors as Immunosuppressive Agents by Structure-Based Virtual Screening", JOURNAL OF MEDICINAL CHEMISTRY, vol. 55, no. 19, 11 October 2012 (2012-10-11), US, pages 8341 - 8349, XP055643334, ISSN: 0022-2623, DOI: 10.1021/jm300630p *

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US20230146096A1 (en) 2023-05-11
WO2021204985A1 (fr) 2021-10-14
ES2928418T3 (es) 2022-11-17
EP3892268B1 (fr) 2022-08-17

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